On the Hollywood red carpets, we expect our A-list stars to be impeccably dressed, to always look timeless and glamorous—but how boring would that be? Luckily, this year, a few celebrities got the fun memo; with folks as diverse as Alexander Skarsgard and Rihanna embracing wacky whimsy, and turning up to step and repeats in avant-garde looks that were wild—and entirely unexpected.
Consider this 2025 recap a lesson in embracing individuality. When other stars wore suits and naked gowns; these style savants slipped into outfits that were decidedly more polarizing. Remember when Jaden Smith wore a full-on castle on his head? Or when Emma Stone went camp and [ate …
On the Hollywood red carpets, we expect our A-list stars to be impeccably dressed, to always look timeless and glamorous—but how boring would that be? Luckily, this year, a few celebrities got the fun memo; with folks as diverse as Alexander Skarsgard and Rihanna embracing wacky whimsy, and turning up to step and repeats in avant-garde looks that were wild—and entirely unexpected.
Consider this 2025 recap a lesson in embracing individuality. When other stars wore suits and naked gowns; these style savants slipped into outfits that were decidedly more polarizing. Remember when Jaden Smith wore a full-on castle on his head? Or when Emma Stone went camp and ate popcorn out of her Louis Vuitton pockets? (But, no, do not go calling her a popcorn actress.)
What else made the wackadoodle cut this year? There were some theatrical pregnancy reveals, Chippendale-inspired halter shirt-and-tie combos, and even some throwback couture, too. In other words: This was the year of stars not being afraid to turn heads or have a laugh—and thank god for that, because it is safe to say we all needed it.
Below, scroll on for even more of the wildest—and most unexpected—red carpet moments of 2025.
In October, Alexander Skarsgård promoted his film Pillion wearing a full look from Ludovic de Saint Sernin’s fall 2025 collection. That kinky little white halter top instantly had the internet abuzz.
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At the 2025 Met Gala, all about celebrating Black dandyism, Janelle Monae wore a three-dimensional Thom Browne suit that made one do an instant double take. The trompe-l’œil design was an unexpected—but super cool—take on the tailoring theme of the evening.
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Talk about taking couple style to the next level. This month, Timothée Chalamet and Kylie Jenner hit the premiere of Marty Supreme in matching orange Chrome Hearts leather looks. For a duo that’s typically press-shy, they sure came out with a bang on the red carpet.
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Saturday Night Live is all about getting laughs, so it was only natural that Emma Stone took a comedic approach to fashion for the show’s 50th anniversary back in February. She wore a red pocketed Louis Vuitton gown that was filled with popcorn—and she even carried a box of the snack, too.
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At the 2025 Grammys, Jaden Smith hit the red carpet in a black Louis Vuitton suit—but his theatrical castle headpiece stole the show. It was custom-made by the brand Abodi, which prides itself on creating designs inspired by Transylvanian history. The Grammys carpet embodies the sheer joy of turning heads and making a headline—so such an accessory was not entirely ouf of place.
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At the 2025 VMAs, comedian and actor Meg Stalter defied the odds when she showed up dressed as. . . a Dunkin Donuts coffee cup? She also carried a bedazzled cup from the iconic chain, for extra pizzazz. It made us want a large mocha and some Munchkin donuts stat.
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Chappell Roan is never one to play it safe with her fashion choices, and her 2025 Grammys look was no different. The singer revived an unexpected piece of fashion history whn she wore a striking design from the Jean Paul Gaultier spring 2003 couture collection.
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Couture week is all about extravagance, and Cardi B understod the assignment while attending the fall 2025 Schiaparelli couture show in Paris. Showing up dripping in pearls, the rapper accessorized her look with a live bird (either a crow or a raven—we need an ornithologist to confirm). Both birds have been used as recurring visuals for her latest album, Am I the Drama?
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Andre 3000 was one of the most-discussed looks of the 2025 Met Gala, when he showed up wearing. . . a grand piano. What was the story behind such a design? On his way to The Met, the musician dropped a surprise new EP, 7 Piano Sketches. Hence the tie-in. The piano backpack was made by the design and fabrication company Pink Sparrow, and was modeled after a Steinway Model S baby grand. (The 30-pound piece was made using foam, lauan plywood, and 3D-printed elements.)
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She’s coming out! Diana Ross won the 2025 Met Gala when she stepped out wearing a sweeping white gown, punctuated with crystals and beads, that featured an 18-foot train embroidered with the names of her children and grandchildren. Ross’s commanding design was brought to life from a close collaboration between Ross, her son Evan, and Nigerian designer Ugo Mozie.
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Sarah Paulson is never one to shy away from a voluminous red carpet design, and her sculptural Marc Jacobs frock at the 2025 Vanity Fair Oscars after-party did not disappoint. Certainly not your safe black LBD.
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The only way Rihanna can outdo herself at a Met Gala, given she is the Queen of the Met? To use her fashion to announce her third pregnancy: That is precisely what the superstar did this year, when she stepped out in a tailored Marc Jacobs look—despite being loosely corseted—confirmed her growing baby bump.
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Kim Kardashian is at such a high level of fame that, it turns out, she does not even need to show her face for spectators to be able to recognize her. At the Academy Museum Gala this year, Kardashian wore a Margiela design that included a dramatic face mask. We wonder if she still did glam (our guess is yes).
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It was the jaunty little chapeau that had everyone talking: At the 2025 Golden Globes, Succession star Jeremy Strong made waves when he hit the red carpet in a teal Loro Piana suit, complete with the matching bucket hat. It ruled. It was an extremely quirky choice for what is usually a more restrained, formal Hollywood event.
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At the 2025 Met Gala, The Substance star Demi Moore played into the theme of tailoring and dandyism—with an avant-garde Thom Browne look that transformed her into a human tie. A star who dedicates themselves to performance art is a winner in our books.
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Cole Escola won Best Leading Actor (for Oh, Mary!) at the 2025 Tony Awards—and their corseted Wiederhoeft gown was just as exciting. Escola paid tribute to Broadway legend Bernadette Peters, by replicating a dress Peters wore to the Tonys back in 1999. Who doesn’t love a fashion revival?
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Wearing Dilara Findikoglu, Cate Blanchett embraced mermaidcore—who would have thought?—for the Serpentine Gallery Summer Party in London this summer. The bold design included a shapely corset made of entirely of various spiked seashells. It was giving high-fashion sea creature, in the best way possible.
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